DCP-Bio1 is a dimedone-based, sulfenic acid-reactive compound containing a biotin tag, making it compatible with several techniques and forms of analysis for identifying redox-regulated proteins and their specific sites of modification.
Redox-sensitive cysteine residues in proteins may serve as important components of oxidative signaling or sensors of oxidative stress. Cysteine sulfenic acid modification is an emerging area of interest for those studying biological signal transduction within the cell.
Cysteine sulfenic acid formation in proteins results from the oxidative modification of susceptible cysteine residues by signaling-relevant cellular oxidants such as hydrogen peroxide, lipid hydroperoxides and peroxynitrite. These sulfenic acid-modified proteins can be identified by their ability to form adducts with dimedone, but this reagent provides no spectral or affinity tag.
DCP-Bio1 can be used to detect the formation of cysteine sulfenic acid as a common initial step in the redox regulation of proteins, and with the presence of a biotin label, DCP-Bio1 is compatible with several techniques and forms of analysis post-labeling.
Added to intact cells, lysates or protein samples to trap oxidized cysteines chemically, this reagent can be used to study single proteins in isolation or in the context of cells or proteomics-wide protein oxidation in systems of interest.
- Contains biotin tag as affinity handle; no need for ‘click’ chemistry before detection or protein isolation
- Stable, reproducible covalent binding to cysteine sulfenic acid (-SOH) at pH 6.0 – pH 8.0
- Ester linkage stays intact under physiological conditions, but allows for efficient hydrolysis using NH4OH
(Doesn’t hydrolyze under physiological conditions)
- Effective in in vitro and in vivo studies
- Compatible with Western Blotting, ELISA, and Affinity Isolation and cell-imaging techniques
Full Name: DCP-Bio1; 3-(2,4-dioxocyclohexyl)propyl 5-((3aR,6S,6aS)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanoate
Chemical Formula: C19H28N2O5S
Molecular Weight: 396.5 g/mol
Purity: >98% pure
Solubility: At least 500 mM in DMSO, at least 5 mg/ml in acetonitrile
Stability: Stable > 6 months at -20° C
Spectral Information: No visible absorbance
Storage: Room temperature for short term, -20° C for long term
Comments: Stock solution in DMSO can be added to buffers. Can dissolve in acetonitrile to aliquot and redry.
Leslie B. Poole, PhD, Department of Biochemistry
Bruce King, PhD, Departments of Biochemistry and Chemistry
Poole, et al. (2007) Fluorescent and affinity-based tools to detect cysteine sulfenic acid formation in proteins. Bioconjug Chem 18, 2004-17.
Klomsiri, C., et al. (2010) Use of dimedone-based chemical probes for sulfenic acid detection: evaluation of conditions affecting probe incorporation into redox-sensitive proteins. Methods Enzymol 473, 77-94.
Nelson, K.J., et al. (2010) Use of dimedone-based chemical probes for sulfenic acid detection; methods to visualize and identify labeled proteins. Methods Enzymol 473, 95-115.
Redox regulation, protein oxidation, cysteine sulfenic acid
Peter Golikov, MS, MBA, CLP
Licensing Director, Center for Technology Innovation & Commercialization
Ref #: WFU 13-17